• Title/Summary/Keyword: new sesquiterpene lactone

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The study of chemical substances in Hymenoxys brachyactis(II) (Hymenoxys brachyactis의 화학성분에 관한 연구(II))

  • Lee, Sang-Jun;Kim, Sung-Han;Kim, Jung-Han
    • Applied Biological Chemistry
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    • v.38 no.5
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    • pp.473-477
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    • 1995
  • The dichloromethane extracts of the above ground parts of Hymenoxys brachyactis afforded three sesquiterpene lactones already reported, one new sesquiterpene lactone, biennin C and hispidulin as known toxic flavone. Structures of all compounds were established by spectroscopy and biennin C was determined as an adduct of the modified pseudoguanolide and hymenoxon by Gas Chromatograpy and MS spectrometer These sesquiterpene lactones have the same ${\alpha},{\beta}$-unsaturated functional group like that of hymenovin which has been known as major toxic constituent of important livestock poison. And biennin C is also considered as toxic compound because of toxic hymenoxon.

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A New Sesquiterpene Lactone from Artemisia rubripes Nakai

  • Lee, Kyu-Ha;Min, Yong-Deuk;Choi, Sang-Zin;Kwon, Hak-Cheol;Cho, Ock-Ryun;Lee, Kang-Choon;Lee , Kang-Ro
    • Archives of Pharmacal Research
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    • v.27 no.10
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    • pp.1016-1019
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    • 2004
  • The chromatographic separation of a methylene chloride extract of Artemisia rubripes led to the isolation of a new sesquiterpene lactone (3), together with four known compounds, a coumarin (2) and three terpenes (1, 4, and 5). Their structures were characterized to be $1{\beta},6{\alpha}$- dihydroxy-4(15)-eudesmene (1), scopoletin (2), $1{\alpha},4{\beta}-dihydroxy-8{\alpha}$-acetoxy-guaia-2,10(14), 11(13)-triene-6,12-olide (3), $1{\alpha},4{\beta}$ -dihydroxy-8${\alpha}$-acetoxy-guaia-2,9,11(13)-triene-6,12-olide (4), and $\beta$ -sitosterol-3-O-${\beta}$-D-glycoside (5) by spectroscopic means.

Chemical Constituents and Biological Activities of Cichorium intybus L.

  • El-Lakany, Abdalla M.;Aboul-Ela, Maha A.;Abdul-Ghani, Mohamed M.;Mekky, Hattem
    • Natural Product Sciences
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    • v.10 no.2
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    • pp.69-73
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    • 2004
  • Continuation of a phytochemical study of Cichorium intybus L. (Astraceae) growing in Egypt, resulted in the isolation and identification of a new sesquiterpene lactone 3,4-dihydrolactucin, in addition to the eight known compounds; kaempferol, isoscutellarin, cichoriin, umbelliferone, lupeol, lupeol acetate, ${\beta}-sitosterol$, and ${\beta}-sitosterol-3-O-glucoside$. Chemical structures of the isolated compounds were assigned based on different physical, chemical, and spectroscopic techniques including IR, UV, MS, 1D- and 2D-NMR spectra. Furthermore, the antimicrobial, and spasmogenic activities of some fractions and isolates were also assessed.

Dentatins: Sesquiterpene Glucosides from lxeris dentata

  • Chung, Ha-Sook;Woo, Won-Sik;Lim, Sook-Ja
    • Archives of Pharmacal Research
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    • v.17 no.5
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    • pp.323-326
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    • 1994
  • Three new sesquiterpene lactone glucosides named dentatins A, B and C were isolated from lxeris dentata and the structures were elucidated as $3{\betha}, {\;}8{\betha}-dihydroxy-(1{\alpha}, 5{\alpha})guainan-10(14)-ene-6{\alpha}, {;\}12-olide-3-O-{\betha}-D-giucopyuranoside{\;}(1), {\;}3{\betha}, {\;}8{\betha}-dihydroxy-(1{\alpha}, {\;}5{\alpha})-guaian-4(15), {\;}10(14)-diene-6{\alpha}, {\;}12-plide-3-O-{\betha}-D-glucopyranoside{\;}(3)$, respectively, on the basis of spectral evidence.

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Cytotoxic Constituents of the Leaves of Ixeris sonchifolia

  • Suh, Ji-Young;Jo, Young-Mi;Kim, Nam-Deuk;Bae, Song-Ja;Jung, Jee-H.;Im, Kwang-Sik
    • Archives of Pharmacal Research
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    • v.25 no.3
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    • pp.289-292
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    • 2002
  • The ethyl acetate extract of the leaves of Ixeris sonchifolia afforded two new and two known sesquiterpene lactone glucosides of the guaiane-type, together with a known alkenol glucoside. The known compounds were identified as ixerin Z (1), ixerin Z-6'-p-hydroxyphenylace-tate (2), and (Z)-3-hexen-1-ol-$\beta$-D-glucopyranoside (3), respectively. The structures of the new compounds were elucidated as 11, 13a-dihydroixerin Z [4, 3-hydroxy-2-oxo-guaia-1 (10), $3-dien-5{\alpha},6{\beta},7{\alpha},11{\beta}H-12,6-olide-3-O-{\beta}-D-glucopyranoside],{\;}and{\;}3,10{\$beta}-dihydroxy-2-oxo-guaia-3,11(13)-dien-1{\alpha},5{\alpha},6{\alpha},7aH-12,6-olide-10-O-{\beta}-D-glucopyranoside$ (5), respectively. The cytotoxicity of these compounds against human hepatocellular carcinoma cell (HepG2) and human melanoma cell (SK-MEL-2) was evaluated.

Inhibition of Human Neutrophil Elastase by Sesquiterpene Lactone Dimers from the Flowers of Inula britannica

  • Kim, Kwan-Chul;Kim, Dae-Jung;Lee, Myung Sun;Seo, Ji Yun;Yoo, Ick-Dong;Lee, Ik-Soo
    • Journal of Microbiology and Biotechnology
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    • v.28 no.11
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    • pp.1806-1813
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    • 2018
  • A new sesquiterpene lactone dimer [1], together with five known compounds (2-6), was isolated from the flowers of Inula britannica. The structures of these compounds were established by extensive spectroscopic studies and chemical evidence. The inhibitory activities of these isolated compounds (1-6) against human neutrophil elastase (HNE) were also evaluated in vitro; compounds 1 and 6 exhibited significant inhibitory effects against HNE activity, with $IC_{50}$ values of 8.2 and $10.4{\mu}m$, respectively, comparable to that of epigallocatechin gallate (EGCG; $IC_{50}=10.9{\mu}M$). In addition, compounds 3 and 5 exhibited moderate HNE inhibitory effects, with $IC_{50}$ values of 21.9 and $42.5{\mu}M$, respectively. In contrast, compounds 2 and 4 exhibited no such activity ($IC_{50}$ > $100{\mu}M$). The mechanism by which 1 and 3 inhibited HNE was noncompetitive inhibition, with inhibition constant ($K_i$) values of 8.0 and $22.8{\mu}M$, respectively.

Yomogin, an Inhibitor of Nitric Oxide Production in LPS-Activated Macrophages

  • Ryu, Jae-Ha;Lee, Hwa-Jin;Jeong, Yeon-Su;Ryu, Shi-Yong;Han, Yong-Nam
    • Archives of Pharmacal Research
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    • v.21 no.4
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    • pp.481-484
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    • 1998
  • In activated macrophages the inducible form of nitric oxide synthase (i-NOS) generates high amounts of toxic mediator, nitric oxide (NO) which contributes to the circulatory failure associated with septic shock. A sesquiterpene lactone compound (yomogin) isolated from medicinal plant Artemisia princeps Pampan inhibited the production of NO in LPS-activated RAW 264.7 cells by suppressing i-NOS enzyme expression. Thus, yomogin may be a useful candidate for the development of new drugs to treat endotoxemia and inflammation accompanied by the overproduction of NO.

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Sesquiterpene Lactones: A Review of Biological Activities (세스퀴테르펜 락톤류: 생리활성 재검토)

  • Karadeniz, Fatih;Oh, Jung Hwan;Kong, Chang-Suk
    • Journal of Life Science
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    • v.31 no.4
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    • pp.430-441
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    • 2021
  • Sesquiterpene lactones (STLs) are terpenoids found mostly in the Asteraceae family and are known for their strong cytotoxic properties, among other notable bioactivities. Some STLs, such as artemisinin and mipsagargin, are already commercially available and are used to fight malaria and tumor growth, respectively. Although the interest in STLs was low for a time after their discovery due to their toxic nature, past decades have witnessed a soar in STL-based studies focused on developing novel pharmaceuticals via chemical diversification. These studies have reported several promising physiological effects for STLs, including lower toxicity and diverse modes of action, and have demonstrated the antimicrobial, antioxidant, hepatoprotective, antiviral, antiprotozoal, phytotoxic, antitumor, and antiaging properties of STLs. STLs are mainly considered as valuable natural molecules for the fight against cancer since most STLs induce death of different types of cancer cells, as shown by in vitro and in vivo studies. Some STLs can also enhance the effects of drugs that are already in clinical use. Medicinal chemists use various STLs as starting molecules for the synthesis of new STLs or different bioactive compounds. All these developments warrant future research to provide more information on STLs, their bioactivities, and their mode of action. In this context, this review has summarized the bioactivities of some of the widely studied STLs, namely artemisinin, costunolide, thapsigargin, arglabin, parthenolide, alantolactone, cynaropicrin, helenalin, and santonin.